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I need help getting started

Hi! I haven't been to the Caribbean since my honeymoon 20 years ago when my husband and I had a fabulous time in Grenada.

Now we are ready to go back and are taking 16 year old twin boys with us.

We should have use of frequent flier miles, and assuming travel is free, I would like to keep the vacation under 10k for a week in February. A little less would be nice, and I know this is an expensive time of year to do it. I preferred Christmas until I saw what THAT would cost.

I know that isn't really a luxury vacation, and we aren't going to be staying at Caneel Bay (sob!)

I think my instinct is to economize on accommodations so that we can spend more money on activities. My kids love nature and love to see and do new things. They aren't going to want clubs/casinos/shopping. They will want to charter a boat for off shore snorkeling or rent kayaks and explore the shoreline. I can't see us being happy at a big resort. But then I start thinking about how nice a fancy pool would be, how lovely it would be to not have to think about food, and how they might have free activities my kids would like. So then I doubt myself.

I have been looking at vacation rentals on St. John, which I think we would all love because of the National Park and good snorkeling from the beach. But so many of the rentals appear to be up in the hills, and having to drive to get to the beach sounds (1) like a drag for the adults, whose suburban lives involve too much driving as it is and (2) restrictive for the boys, who if staying right on the beach could just take off together without us. I am sure where ever we go we will rent a car, but I would prefer not to have to use it every time we want to do something.

I think in the end, I would love a nice but not fancy place to stay on an Island that is sort of "easy" to be on - not too many hoards of people, not too many obnoxious vendors, easy access to nice beaches, safe, relatively easy to get to from the East Coast of the US, etc. We probably would ideally like to be somewhere near enough to a few less expensive restaurants with good local food. We loved how friendly Grenada was and how good the cheapest street food was. It is kind of a hike to get there, though, when we only have seven days.

Specific ideas about where I should look would be welcome, but also if anyone just wants to give wisdom on how to prioritize when planning a vacation to the Islands would be nice. Thank you in advance!

I read your post a couple of hours ago and had to think a bit before I responded. Now, I'm not trying to sound condescending but if you re-read what you wrote you'll see you have some great ideas but then you've managed to come up with reasons why those ideas won't work for you. I believe that's why you are having difficulty "getting started".

I realize that everyone wants a "perfect" vacation but most seasoned travelers know any vacation is really a series of compromises (some big, some small). If you are open enough to make some compromises you'll find it much easier to find YOUR PLACE IN THE SUN.

Now for what I hope are some helpful suggestions.

First, you indicated a desire to use frequent flyer miles for your airfare. Since you are planning to travel in February this may prove difficult if you are planning to go during President's Week or actually using FF miles (i.e. miles earn with a specific airline that restrict you to that airline or it's partners) as opposed to "points" earned with a travel card that, in effect, allow you to purchase a ticket on any airline. The former often have blackout dates (usually around peak travel times like major holidays) or are limited to only a few seats on each flight that they get booked 330 days in advance or end up costing more "miles" than one has in their account. The upshot being FF award tickets are not always available for every destination. For example, you might be planning to fly to St. Thomas only to find out there are no FF Award seats for the day(s) you want to travel but you can get seats to perhaps Aruba. If that happens all your "St. Thomas planning" goes out the window. So, you'll have to first determine where you can reasonably expect get to using your FF miles. On the other hand if you are using points from a travel rewards card to purchase your tickets you'll have more options.

Your instincts are correct in that you'll find better accommodations value if you stay in a villa or condo rather than a resort, so concentrate your search there. Almost all condos and many villas will have pools so that should be an issue and I would let the availability of "on site food" be a major factor in your decision of where to stay. If you are in a condo/villa you can easily stock the pantry with provisions for breakfast, lunch and snacks yet still go out for a few meals when the desire strikes.

St. John is a great island for families with teenagers for all of the reasons you already mentioned. Simply because there are no beachfront rentals is not a reason to cross it off your list as the advantages far outweigh the minor inconvenience of getting into your rental car for a short drive - it's really not the big of a deal.

Another island you might want to look at is Providenciales in the Turks & Caicos - check out the numerous "condo resorts" on Grace Bay. You'll be situated on 11+ miles of the whitest sand beach you can imagine and you'll have all the advantages of staying in a private multi-bedroom condo with access resort type amenities like pools, on-site restaurants and perhaps children's/teenage programs. Of course, you can also rent private villas around the island.

There are lots of condo type resorts and rental villas on St. Martin. The island is relatively easy to reach with non-stop flights from numerous US International airports, there's all types of activities that would interest your teenagers, however, it will be a somewhat crowded island.

Look also at St. Kitts. It is still somewhat undiscovered so you won't find "hordes of people" yet it offers plenty of rental condo's and villas. Snorkeling is somewhat limited but there are plenty of other activities that will keep your teenagers occupied. It is reachable non-stop from a few East Coast US airports.

If you concentrate your efforts on identifying the "pluses" of an island rather than dwelling on why something "won't work" you'll find it much easier to a place to enjoy while you are on vacation. As far as I'm concerned, there's really no "bad" place in the Caribbean, only "different" places and VIVA LA DIFFERENCE!!!!

Thank you so much for your reply. It was very helpful, and you are certainly right that I may be over thinking this!

I will check out the Turks and Caicos. Thank you for that tip.

We will be traveling on "points" through our credit card. We are not limited to a particular airline, but I will check about whether there are black out dates. That is definitely something to find out ahead of time.

I know that where ever we choose, we can have a great vacation, so thank you for reminding me to focus on the positives of any particular set of compromises. I think in the end, I will be ok with compromises - I don't feel particular rigid about having to have perfect accommodations or perfect food, but I definitely struggle with having to make concrete choices! When looking at an island vacation, the sum of all the options it just .... so attractive! It's hard to choose one thing and let the others all go, but perhaps ultimately we just need to travel more so that too much is not required of any particular trip.

you might take a look at provo in turks & caicos. it's a small island & was british so easy to navigate. has super snorkeling (walkin & by boat). the island has loads of villas it you choose that - this villa is an easy walk to 6 restaurants, dive shop, turtle cove marina & maybe 5 min walk down the beach to the best walkin snorkel on island: http://www.bellasurmer.com/
you would still need a car for restaurants, groceries, etc.

alternatively there are numerous condo style resorts. these have pools, restaurants, some activities with units that have porch/balcony & full kitchens - which might work well with the twins. you can economize by sometimes having coffee, cocktails, breakfast or lunch in room. lots of price ranges. car also needed for resorts although drive times will not likely exceed 10 mins resort to restaurant. all the resorts are beachfront.

I completely agree with RoamsAround. He has given you great advice. I also understand your desire to be on or within walking distance to a beach, especially with teenagers. I much prefer being on the beach rather than having to drive. St. John has tons of villas for rent but then you have to drive to the beach.

I think the French side of St. Martin ticks most of your boxes except for the not crowded part. But if you stayed at someplace like the Grand Case Beach Club then you'll have a quiet beach right next door. They also have 2-bedroom accommodations with kitchens and the resort is within walking distance of the great restaurants in Grand Case. It's about a 10-15 minute drive to the very busy Orient Beach where there are lots of beach restaurants/bars/watersports (and also topless women if that matters to you).

Alternatively, if you want to be right on Orient Beach there are lots of different accommodations just behind the beach. There's a small village area (Orient Village) with a few restaurants and a small convenience-type store (Tap 5). There are condo-type resorts and hotels.

Here's an example of what is available at Orient Village (this is not an endorsement of the villa nor the agency. It's just an example for information purposes. I have not stayed here.):

Another reason I prefer St. Martin over Turks & Caicos in February is that St. Martin is a bit farther south than T&C. I like T&C and I think it would be a good choice for you since most of the accommodations are condo-style and the beach is stunning. But personally, I would go further south than T&C from about December - February because I don't want to chance not having warm weather for my beach vacation.

We were just in Grenada in November and loved it. But we like St. Martin, too and have been a few times. It's easy to reach and has a little bit of everything.

Before you get sold on any one island, I would back up and see where your FF miles can get you first. What islands offer the best flights, times, connections, etc. and are available using the FF in your timeframe.

I have to agree, before spending time debating on destinations, I would see where my FF miles will actually get me.

From your comments, it seems you have St. John on the top of your list. There are other places to stay there besides Caneel Bay.

T & C would be a great choice. There are several condo units and resorts right on Grace bay beach. No need to worry about going up and down a mountain to get to one of the best beaches in the Caribbean. However, you really do need to rent a car there just to get around and see the Island as well as a variety of dining options.